diff --git a/extensions/telegram/src/monitor.ts b/extensions/telegram/src/monitor.ts
index e703266f0f0..6ff2e8ef9d0 100644
--- a/extensions/telegram/src/monitor.ts
+++ b/extensions/telegram/src/monitor.ts
@@ -91,8 +91,10 @@ export async function monitorTelegramProvider(opts: MonitorTelegramOpts = {}) {
     const activeRunner = pollingSession?.activeRunner;
     if (isNetworkError && isTelegramPollingError && activeRunner && activeRunner.isRunning()) {
       pollingSession?.markForceRestarted();
+      pollingSession?.markTransportDirty();
       pollingSession?.abortActiveFetch();
       void activeRunner.stop().catch(() => {});
+      log("[telegram][diag] marking transport dirty after polling network failure");
       log(
         `[telegram] Restarting polling after unhandled network error: ${formatErrorMessage(err)}`,
       );
@@ -180,9 +182,11 @@ export async function monitorTelegramProvider(opts: MonitorTelegramOpts = {}) {
     }
 
     // Create transport once to preserve sticky IPv4 fallback state across polling restarts
-    const telegramTransport = resolveTelegramTransport(proxyFetch, {
-      network: account.config.network,
-    });
+    const createTelegramTransportForPolling = () =>
+      resolveTelegramTransport(proxyFetch, {
+        network: account.config.network,
+      });
+    const telegramTransport = createTelegramTransportForPolling();
 
     pollingSession = new TelegramPollingSession({
       token,
@@ -196,6 +200,7 @@ export async function monitorTelegramProvider(opts: MonitorTelegramOpts = {}) {
       persistUpdateId,
       log,
       telegramTransport,
+      createTelegramTransport: createTelegramTransportForPolling,
     });
     await pollingSession.runUntilAbort();
   } finally {
diff --git a/extensions/telegram/src/polling-session.ts b/extensions/telegram/src/polling-session.ts
index 9b92435f4ec..15690b3a34d 100644
--- a/extensions/telegram/src/polling-session.ts
+++ b/extensions/telegram/src/polling-session.ts
@@ -50,6 +50,8 @@ type TelegramPollingSessionOpts = {
   log: (line: string) => void;
   /** Pre-resolved Telegram transport to reuse across bot instances */
   telegramTransport?: TelegramTransport;
+  /** Rebuild Telegram transport after stall/network recovery when marked dirty. */
+  createTelegramTransport?: () => TelegramTransport;
 };
 
 export class TelegramPollingSession {
@@ -58,8 +60,12 @@ export class TelegramPollingSession {
   #forceRestarted = false;
   #activeRunner: ReturnType<typeof run> | undefined;
   #activeFetchAbort: AbortController | undefined;
+  #telegramTransport: TelegramTransport | undefined;
+  #discardTransportOnRestart = false;
 
-  constructor(private readonly opts: TelegramPollingSessionOpts) {}
+  constructor(private readonly opts: TelegramPollingSessionOpts) {
+    this.#telegramTransport = opts.telegramTransport;
+  }
 
   get activeRunner() {
     return this.#activeRunner;
@@ -69,6 +75,10 @@ export class TelegramPollingSession {
     this.#forceRestarted = true;
   }
 
+  markTransportDirty() {
+    this.#discardTransportOnRestart = true;
+  }
+
   abortActiveFetch() {
     this.#activeFetchAbort?.abort();
   }
@@ -126,6 +136,15 @@ export class TelegramPollingSession {
   async #createPollingBot(): Promise<TelegramBot | undefined> {
     const fetchAbortController = new AbortController();
     this.#activeFetchAbort = fetchAbortController;
+    const shouldRebuildTransport = this.#discardTransportOnRestart || !this.#telegramTransport;
+    const telegramTransport = shouldRebuildTransport
+      ? (this.opts.createTelegramTransport?.() ?? this.#telegramTransport)
+      : this.#telegramTransport;
+    if (shouldRebuildTransport && telegramTransport) {
+      this.opts.log("[telegram][diag] rebuilding transport for next polling cycle");
+    }
+    this.#telegramTransport = telegramTransport;
+    this.#discardTransportOnRestart = false;
     try {
       return createTelegramBot({
         token: this.opts.token,
@@ -138,7 +157,7 @@ export class TelegramPollingSession {
           lastUpdateId: this.opts.getLastUpdateId(),
           onUpdateId: this.opts.persistUpdateId,
         },
-        telegramTransport: this.opts.telegramTransport,
+        telegramTransport,
       });
     } catch (err) {
       await this.#waitBeforeRetryOnRecoverableSetupError(err, "Telegram setup network error");
@@ -186,11 +205,49 @@ export class TelegramPollingSession {
     await this.#confirmPersistedOffset(bot);
 
     let lastGetUpdatesAt = Date.now();
-    bot.api.config.use((prev, method, payload, signal) => {
-      if (method === "getUpdates") {
-        lastGetUpdatesAt = Date.now();
+    let lastGetUpdatesStartedAt: number | null = null;
+    let lastGetUpdatesFinishedAt: number | null = null;
+    let lastGetUpdatesDurationMs: number | null = null;
+    let lastGetUpdatesOutcome = "not-started";
+    let lastGetUpdatesError: string | null = null;
+    let lastGetUpdatesOffset: number | null = null;
+    let inFlightGetUpdates = 0;
+    let stopSequenceLogged = false;
+    let stallDiagLoggedAt = 0;
+
+    bot.api.config.use(async (prev, method, payload, signal) => {
+      if (method !== "getUpdates") {
+        return prev(method, payload, signal);
+      }
+
+      const startedAt = Date.now();
+      lastGetUpdatesAt = startedAt;
+      lastGetUpdatesStartedAt = startedAt;
+      lastGetUpdatesOffset =
+        payload && typeof payload === "object" && "offset" in payload
+          ? ((payload as { offset?: number }).offset ?? null)
+          : null;
+      inFlightGetUpdates += 1;
+      lastGetUpdatesOutcome = "started";
+      lastGetUpdatesError = null;
+
+      try {
+        const result = await prev(method, payload, signal);
+        const finishedAt = Date.now();
+        lastGetUpdatesFinishedAt = finishedAt;
+        lastGetUpdatesDurationMs = finishedAt - startedAt;
+        lastGetUpdatesOutcome = Array.isArray(result) ? `ok:${result.length}` : "ok";
+        return result;
+      } catch (err) {
+        const finishedAt = Date.now();
+        lastGetUpdatesFinishedAt = finishedAt;
+        lastGetUpdatesDurationMs = finishedAt - startedAt;
+        lastGetUpdatesOutcome = "error";
+        lastGetUpdatesError = formatErrorMessage(err);
+        throw err;
+      } finally {
+        inFlightGetUpdates = Math.max(0, inFlightGetUpdates - 1);
       }
-      return prev(method, payload, signal);
     });
 
     const runner = run(bot, this.opts.runnerOptions);
@@ -236,11 +293,26 @@ export class TelegramPollingSession {
       if (this.opts.abortSignal?.aborted) {
         return;
       }
-      const elapsed = Date.now() - lastGetUpdatesAt;
+
+      const now = Date.now();
+      const activeElapsed =
+        inFlightGetUpdates > 0 && lastGetUpdatesStartedAt != null ? now - lastGetUpdatesStartedAt : 0;
+      const idleElapsed = inFlightGetUpdates > 0 ? 0 : now - (lastGetUpdatesFinishedAt ?? lastGetUpdatesAt);
+      const elapsed = inFlightGetUpdates > 0 ? activeElapsed : idleElapsed;
+
       if (elapsed > POLL_STALL_THRESHOLD_MS && runner.isRunning()) {
+        if (stallDiagLoggedAt && now - stallDiagLoggedAt < POLL_STALL_THRESHOLD_MS / 2) {
+          return;
+        }
+        stallDiagLoggedAt = now;
+        this.#discardTransportOnRestart = true;
         stalledRestart = true;
+        const elapsedLabel =
+          inFlightGetUpdates > 0
+            ? `active getUpdates stuck for ${formatDurationPrecise(elapsed)}`
+            : `no completed getUpdates for ${formatDurationPrecise(elapsed)}`;
         this.opts.log(
-          `[telegram] Polling stall detected (no getUpdates for ${formatDurationPrecise(elapsed)}); forcing restart.`,
+          `[telegram] Polling stall detected (${elapsedLabel}); forcing restart. [diag inFlight=${inFlightGetUpdates} outcome=${lastGetUpdatesOutcome} startedAt=${lastGetUpdatesStartedAt ?? "n/a"} finishedAt=${lastGetUpdatesFinishedAt ?? "n/a"} durationMs=${lastGetUpdatesDurationMs ?? "n/a"} offset=${lastGetUpdatesOffset ?? "n/a"}${lastGetUpdatesError ? ` error=${lastGetUpdatesError}` : ""}]`,
         );
         void stopRunner();
         void stopBot();
@@ -270,6 +342,9 @@ export class TelegramPollingSession {
           ? "unhandled network error"
           : "runner stopped (maxRetryTime exceeded or graceful stop)";
       this.#forceRestarted = false;
+      this.opts.log(
+        `[telegram][diag] polling cycle finished reason=${reason} inFlight=${inFlightGetUpdates} outcome=${lastGetUpdatesOutcome} startedAt=${lastGetUpdatesStartedAt ?? "n/a"} finishedAt=${lastGetUpdatesFinishedAt ?? "n/a"} durationMs=${lastGetUpdatesDurationMs ?? "n/a"} offset=${lastGetUpdatesOffset ?? "n/a"}${lastGetUpdatesError ? ` error=${lastGetUpdatesError}` : ""}`,
+      );
       const shouldRestart = await this.#waitBeforeRestart(
         (delay) => `Telegram polling runner stopped (${reason}); restarting in ${delay}.`,
       );
@@ -284,11 +359,17 @@ export class TelegramPollingSession {
         this.#webhookCleared = false;
       }
       const isRecoverable = isRecoverableTelegramNetworkError(err, { context: "polling" });
+      if (isConflict || isRecoverable) {
+        this.#discardTransportOnRestart = true;
+      }
       if (!isConflict && !isRecoverable) {
         throw err;
       }
       const reason = isConflict ? "getUpdates conflict" : "network error";
       const errMsg = formatErrorMessage(err);
+      this.opts.log(
+        `[telegram][diag] polling cycle error reason=${reason} inFlight=${inFlightGetUpdates} outcome=${lastGetUpdatesOutcome} startedAt=${lastGetUpdatesStartedAt ?? "n/a"} finishedAt=${lastGetUpdatesFinishedAt ?? "n/a"} durationMs=${lastGetUpdatesDurationMs ?? "n/a"} offset=${lastGetUpdatesOffset ?? "n/a"} err=${errMsg}${lastGetUpdatesError ? ` lastGetUpdatesError=${lastGetUpdatesError}` : ""}`,
+      );
       const shouldRestart = await this.#waitBeforeRestart(
         (delay) => `Telegram ${reason}: ${errMsg}; retrying in ${delay}.`,
       );